#6. DMT

SYNTHESIS : (from N,N,N-trimethyltryptammonium iodide,
dimethyltryptamine methiodide, DMT·CH3I): This quaternary salt is
prepared from tryptamine and methyl iodide. To a stirred solution of 3
g tryptamine in 30 mL IPA there was added 10 g methyl
iodide. Cream-colored solids appeared immediately and, after 12 h
stirring at room temperature, these were removed by filtration, washed
twice with IPA and warm isopropanol, and air dried to constant
weight. There was thus obtained 1.81 g N,N,N-trimethyltryptammonium
iodide. Recrystallization of an analytical sample using acetonitrile
gave a white crystalline product with a mp of 210-211 °C. IR (in
cm-1): 767, 919, 953, 978, 1105, with a sharp stretch at 3400. In
principle, DMT is contained in the filtrate along with NMT and
tryptamine itself. The tryptamine can be removed based on its ether
insolubility and the NMT by its conversion to the benzamide with
acetic anhydride or benzoyl chloride. The remaining basic material is
largely DMT which can be further purified as the picrate salt. The
yield is minuscule, and better results are obtained by the
demethylation of this salt.

The demethylation of the iodide salt: Under an inert atmosphere, a
solution of 0.40 g N,N,N-trimethyltryptammonium iodide in 5 mL THF was
treated with 1.5 mL of 1M LiEt3BH in THF and held at reflux
temperature for 9 h. After cooling, the mixture was acidified with
dilute HCl and the THF removed under vacuum. The residue was suspended
in dilute NaOH and extracted with Et2O. The extracts were pooled, and
the solvent removed under vacuum to provide a residue of 0.12 g
N,N-dimethyltryptamine (DMT) as a crystalline solid, with a mp of
57-59 °C. IR (in cm-1): 732, 740, 811, 859, 1011, 1037, 1110,
1171. The MS is discussed below.

The demethylation of the chloride salt: A hot aqueous solution of
N,N,N-trimethyltryptammonium iodide was treated with an excess of
freshly precipitated AgCl, and all was boiled gently for 15 min. The
mixed silver halides were removed by filtration, and the filtrate
stripped of H2O as rapidly as possible. To the residue there was added
a small amount of MeOH follow by acetone until the crystallization of
N,N,N-trimethyltryptammonium chloride was complete. It had a mp of 193
°C (80%), and it is considerably more water soluble than the
starting iodide. This salt was pyrolysed under hard vacuum and the
residue distilled. This distillate was dissolved in a small amount of
methanol and acidified with dilute nitric acid. A small amount of
insoluble material was removed by filtration, the aqueous phase washed
with CHCl3, made basic with aqueous NaOH, and extracted with
CHCl3. The solvent was removed under vacuum, and the residue treated
with a hot solution of picric acid. This was decanted from a little
insoluble material, and slowly cooled to provide the picrate of DMT as
yellow needles with a mp of 167 °C. An aqueous suspension of this
picrate was made basic with an excess of aqueous NaOH, extracted with
Et2O, and the solvent removed under vacuum to provide a pale yellow
residue that crystallized. This was pressed on a porous plate and
washed with petroleum ether to give N,N-dimethyltryptamine (DMT) as an
off-white solid with a mp of 47 °C.

The demethylation of the thiophenolate salt: A suspension of 2.5 g
N,N,N-trimethyltryptammonium iodide in 25 mL MeOH was brought into
solution by heating, and treated with 1.0 g Ag2O. The mixture was
heated for 10 min on the steam bath, the solids removed by filtration
and washed with an additional 20 mL MeOH. The methanol solutions were
treated with 1.0 g thiophenol and the solvent was removed under
vacuum. The resulting viscous oil (2.12 g) was heated with a flame to
the reflux point and there was extensive bubbling. After 5 min, the
light colored reaction mixture was cooled to room temperature,
dissolved in 50 mL CH2Cl2, and extracted with two 25 mL portions of
dilute HCl. These were pooled (pale yellow color), made basic with 5%
aqueous NaOH and extracted with 3x25 mL CH2Cl2. After removal of the
solvent from the pooled extracts, the residue (an amber oil, 1.04 g)
was distilled at the KugelRohr. A white oil distilled over at 130-140
°C at 0.1 mm/Hg, and crystallized spontaneously. This distillate
weighed 0.77 g, and was recrystallized from boiling hexane after
decanting the solution from a small amount of insolubles. There was
thus obtained 0.40 g of dimethyltryptamine (DMT) with a mp 67-68
°C. The distillate contained about 3% of
2-Methyl-1,2,3,4-tetrahydro-b-carboline (parent peak mass 186, major
peak mass 186) as an impurity which was lost upon
recrystallization.

(from tryptamine and ethyl formate) A suspension of 1.0 g tryptamine
in 50 mL ethyl formate was held at reflux for 15 h during which time
the mixture became homogeneous. The volatiles were removed under
vacuum, yielding an oily residue of the formamide. This may be
purified by distillation but this unpurified product can serve
satisfactorily in the following reaction. This residue was dissolved
in 50 mL anhydrous THF and added, dropwise, to a solution of 1.0 M LAH
in THF (40 mL, 40 mmole) which had been diluted with another 50 mL
THF. After the addition was complete the reaction mixture was heated
under reflux for 15 hours. Reflux was continued as a solution of 40 mL
1.0 M freshly distilled ethyl formate in THF was added dropwise over
the course of 2 h. Heating was discontinued and the reaction mixture
was quenched by the addition of excess solid sodium sulfate
decahydrate at room temperature. The reaction mixture was filtered and
the filtrate was concentrated under vacuum to yield 1.15 g pure
N,N-dimethyltryptamine as an oil which solidified upon storage in the
freezer. The material can be recrystallized from hexane to give white
crystals with a mp 67 °C.

(from indole) To a well stirred solution of 10 g indole in 150 mL
anhydrous Et2O there was added, dropwise over the course of 30 min, a
solution of 11 g oxalyl chloride in 150 mL anhydrous Et2O. Stirring
was continued for an additional 15 min during which time there was the
separation of indol-3-ylglyoxyl chloride as a yellow crystalline
solid. This intermediate was removed by filtration and washed with
Et2O. It deteriorates at a significant rate at room temperature, and
should be used as soon as possible after preparation. The diethylether
in this synthesis can be replaced advantageously with
t-butylmethylether (TBME) which works well as a solvent in this
reaction, but which avoids the potential danger associated with
peroxide formation. The above indol-3-ylglyoxyl chloride was added to
20 g anhydrous dimethylamine in 150 mL cold, stirred anhydrous
Et2O. When the color had largely been discharged, there was added an
excess of 2N HCl, the mixture was cooled, and the resulting solids
were removed by filtration. These were recrystallized from EtOAc to
give, after air drying, 14.6 g (79%) indol-3-yl
N,N-dimethylglyoxylamide with a mp of 159-161 °C.

A solution of 14 g indol-3-yl-N,N-dimethylglyoxylamide in 350 mL
anhydrous THF was added, slowly, to 19 g LAH in 350 mL THF which was
well stirred and held at reflux temperature under an inert
atmosphere. After the addition was complete, reflux was maintained for
an additional 16 h, the reaction mixture cooled, and the excess
hydride destroyed by the cautious addition of wet dioxane. The formed
solids were removed by filtration, washed with hot THF, the filtrate
and washings combined, dried over anhydrous MgSO4, and the solvent
removed under vacuum. The residue was dissolved in hot petroleum
ether. On cooling, crystals of N,N-dimethyltryptamine (DMT) were
formed, filtered free of solvent, and air dried, weighing 11.1 g
(91%). There have been reports of byproducts from this LAH procedure
when performed in Et2O that can compromise the purity of the final
product. To obtain the HCl salt of DMT, the residue was dissolved in
anhydrous Et2O and saturated with anhydrous hydrogen chloride. The
resulting crystals were recrystallized from benzene/methanol to give
N,N-dimethyltryptamine hydrochloride with a mp of 165-167 °C. The
yield from 14 g of the amide was 13.3 g of the salt.

There are several comments to be made as to salts, melting points, and
spectra.

As to salts, this last recipe above, taken from the literature, is the
only claim of a valid hydrochloride salt of DMT. In the original
synthesis, by Manske, the following description appears. "The
hydrochloride could be obtained only as a pale yellow resin which,
when dried in a vacuum desiccator over potassium hydroxide, became
porous and brittle." I have found no attempts at its synthesis in the
literature, and I have personally had no success at all. The picrate
salt is well defined, used mostly for isolation and purification. The
oxalate is used occasionally in animal studies. Early human studies
involving the injection of solutions of the hydrochloride apparently
made by dissolving DMT base in dilute aqueous HCl, and neutralizing
this with base to achieve an end pH of appropriate 6. The fumarate is
the salt specifically approved by the FDA for human studies, and this
was the form used for human intravenous injection employed in the
recent New Mexico studies.

As to melting points, some in the literature are of plant isolates and
other are of synthetic samples. A brief and incomplete survey has
revealed the following numbers, all in °C: 44, 44.6-46.8, 46, 47,
48-49, 49-50, 56-57, 57-59, 58-60, 64-67, 67 and 67-68. The 58-60 and
64-67 values are from the Aldrich Chemical Company, for samples
bearing the purity claims of "puriss" and 99+% "Gold Label" resp. The
Merck Index gives the very early, very low values of 46 °C and
44.6-46.8 °C and claimes that the bp is 60-80 °C with
atmospheric pressure being implied. It is clearly in error on both
matters. No evidence has been published suggesting polymorphism. The
published mp values for the trimethyl quaternary iodide span the range
from 188 °C to 233 °C, including in-between values of 197 °C
and 216-217 °C. This physical property is of limited value.

As to spectra, the EI-MS of DMT presents no surprises. MS (in m/z):
C3H8N+ 58 (100%), indolemethylene+ 130 (10%); parent ion 188 (4%). A
remarkably consistent feature has been mentioned earlier. With
tertiary amines such as DMT, the 130+ mass ion is usually the second
or third most intense in the spectrum. A companion 131+ mass ion is
very small. However, when isomers are observed that may have the same
atomic composition, but which are secondary amines, there is a
prominent 131+ peak, always exceeding the 130+ peak in size. As an
example, NET, with the same molecular weight, had the same major amine
ion fragment at the mass of 58, but at about a half this height is a
130/131 ion pair with the 131+ being the major one. DMT had a CI-MS
(with NH3) with the expected M+1 at mass 189 and a fragment at mass
166.

(with 100 mg, via the buccal mucosa) "Numbness at the site, but no
central effects."

(with 20 mg, intramuscularly) "I began to see patterns on the wall
that were continuously moving. They were transparent, and were not
colored. After a short period these patterns became the heads of
animals, a fox, a snake, a dragon. Then kaleidoscopic images appeared
to me in my inner eye, fantastically beautiful and colored."

(with 60 mg, intramuscularly) "I don't like this feeling -- I am not
myself. I saw such strange dreams a while ago. Strange creatures,
dwarfs or something; they were black and moved about. Now I feel as if
I am not alive. My left hand is numb. As if my heart would not beat,
as if I had no body, no nothing. All I feel are my left hand and
stomach. I don't like to be without thoughts."

(with 75 mg, intramuscularly) "The third or fourth minute after the
injection vegetative symptoms appeared, such as tingling sensation,
trembling, slight nausea, mydriasis, elevation of the blood pressure
and increase of the pulse rate. At the same time, eidetic phenomena,
optical illusions, pseudohallucinations, and later real
hallucinations, appeared. The hallucinations consisted of moving,
brilliantly colored oriental motifs, and later I saw wonderful scenes
altering very rapidly. The faces of people seemed to be masks. My
emotional state was elevated sometimes up to euphoria. At the highest
point I had compulsive athetoid movements in my left hand. My
consciousness was completely filled by hallucinations, and my
attention was firmly bound to them; therefore I could not give an
account of the events happening to me. After 3/4 to 1 hour the
symptoms disappeared, and I was able to describe what had happened.

(with 80 mg, intramuscularly) "My perceptual distortions were visual
in nature and with my eyes closed I could see colored patterns,
primarily geometrical patterns moving very fast, having sometimes very
deep emotional content and connotation. My blood pressure went up and
my pupils were dilated."

(with 30 mg smoked) "I spread it evenly on a joint of Tanacetum
vulgare and melted it with a heat lamp. In about 30 seconds a strong
light-headedness starts, with a feeling of temporal pressure. Some
yellowing of the visual field. There was nothing for me to do because
I had to turn complete control over to the drug. Off the plateau in
3-4 minutes and the fact that the radio was on became apparent. I was
out in a few more minutes."

(with 60 mg smoked) "We did it together. Swift entry -- head
overwhelmed -- elaborate and exotic. Slightly threatening patterns --
no insight -- slight sense of cruelty and sharpness between us, but
enjoying. His face, as before with MDA, demonic but pleasantly so. He
said he saw my face as a mask. He asked me to let him see my teeth. I
laughed -- aware that laughter slightly not-funny. Heavy, massive
intoxication. Time extension extraordinary. What seemed like 2 hrs
was about 30 minutes."

(with 60 mg smoked) "Rapid onset, and in a completely stoned isolation
in about a minute for about three minutes. Slow return but continued
afterglow (pleasant) for thirty minutes. Repeated three times, with no
apparent tolerance or change in chronology. Easily handled. The
intoxication is of limited usefulness but the residues are completely
relaxing,"

(with 100 mg, smoked) "As I exhaled I became terribly afraid, my heart
very rapid and strong, palms sweating. A terrible sense of dread and
doom filled me -- I knew what was happening, I knew I couldn't stop
it, but it was so devastating; I was being destroyed -- all that was
familiar, all reference points, all identity -- all viciously
shattered in a few seconds. I couldn't even mourn the loss -- there
was no one left to do the mourning. Up, up, out, out, eyes closed, I
am at the speed of light, expanding, expanding, expanding, faster and
faster until I have become so large that I no longer exist -- my speed
is so great that everything has come to a stop -- here I gaze upon the
entire universe."

(with 15 mg, intravenously) "An almost instantaneous rush began in the
head and I was quickly scattered. Rapidly moving and intensely colored
visuals were there, and I got into some complex scenes. There were few
sounds, and those that were there were not of anyone talking. I was
able to continue to think clearly."

(with 30 mg, intravenously) "I was hit harder that I had ever been
when smoking the stuff. The onset was similar, but the euphoria was
less."

EXTENSIONS AND COMMENTARY : There is a staggering body of
information on the subject of intoxicating snuffs and their use
throughout the area of the Caribbean, the Amazon, and on to the west,
past the Andes, in Colombia and Peru. The literature that has
accumulated over the last forty or so years is fascinating, but
extremely difficult to organize. The problem lies in deciding on which
discipline shall dictate the hierarchy of classification. Does one
organize by snuff name? But each different tribe will have a different
name. Does one classify by the plants employed? This requires actual
observation in the field, but a given plant may have several native
names. And one snuff may use any of several different plants or plant
combinations, depending on cultural tradition. To add uncertainty to
this complexity, these traditions are being rapidly lost, with the
eradication of folklore. So perhaps one should turn to the snuff
itself, and classify according to the chemical composition. This is
appealing in that there are many museum samples available, as well as
a host of anthropological artifacts such as snuff trays and botanical
residues that can be identified. But that is a luxury that requires
the sophistication of the laboratory, and precludes any botanic
assignment.

No matter which system might eventually prove to be the best, the use
of a chemical assignment of drug structure to the active components
allows some form of clinical challenge to the native use in the
field. DMT and 5-MeO-DMT are the mainstay chemicals in most snuffs,
and can be introduced into the product from any of several plants.

A major plant source for one of the best studied of the snuffs,
cohoba, are the ground beans of the Piptadenia peregrina.
There are two alternative generic names, Anadenanthera and
Mimosa, which may represent the same, or similar, plants, but
this is the stuff for battles between botanical taxonomists. There are
several species in this classification, and the alkaloid content
amongst them is most variable. With P. peregrina and
P. macrocarpa, the major contents of the beans and their pods
appears to be bufotenine, its N-oxide and the oxide of DMT. It may be
only the pods of the seeds that contain the DMT. And the bark seems to
be the major source of N-methyltryptamine, of 5-MeO-NMT (its 5-methoxy
analogue) and of 5-MeO-DMT itself. The species P. colubrina
has been reported to have bufotenine in its seeds as the only active
component. This plant, in Argentina, occurs in only two major species
P. macrocarpa and P. excelsa, and the composition seems
to parallel that of the Amazonian counterparts. Other forms,
(P. rigida, P. paraguayensis, and
P. varidiflora), are without any alkaloid content.

The native intoxicant search becomes even cloudier as one goes from
snuff to decoction. There are several drinks, sometimes described as
"narcotic" and sometimes as hallucinogenic or dream-inducing, that
come from closely related plants. The roots of the acacia-like tree,
Mimosa hostilis, are reputed to be the source of the drink jumera,
or vihno de jurema. But the only alkaloid present, originally called
nigerine, has proved to be DMT, and this is not orally active. There
are pasture grasses, such as reed canarygrass, that can produce a
central nervous system disruption in grazing sheep. Chemical analyses
of these plants (such as Phalaris tuberosa,
P. arundinacea, and P. aquatica ) have revealed the
presence of alkaloids like DMT and 5-MeO-DMT, but these compounds
require intravenous administration to duplicate the toxicity
symptoms. The observation of 5-MeO-NMT being present does not help
explain the toxicity. How can something that is not orally active be
orally active? A possible explanation is the presence of another
indole with a one-carbon shorter chain. This is gramine, or
3-(N,N-dimethylaminomethyl)indole which is synthesized in the plant
with an entirely different set of enzymes. Its human pharmacology is
not known. A related homologue, one carbon longer, is the three-carbon
chain compound 3-[3-(dimethylamino)propyl]indole, produced by the
Upjohn Company. It has been studied clinically under the code name
U-6056, at levels of up to 70 milligrams in 10 subjects, by i.m.
injection. There were no reports of visual, auditory or tactile
disturbances. Physically, there was a slight increase in blood
pressure anad pulse rate. Certainly there were no psychological
effects.

The drink ayahuasca is also a DMT-containing decoction, but the
presence of some harmaline-containing plant is required to make it
active by mouth. This area is discussed under harmaline, although
there is some information to be found in the 5-MeO-DMT commentary
section. And, there are several species of Acacia found in both Africa
and Australia that contain DMT, but there is no native medical use
that suggests psychotropic action. Most of this is part and parcel of
the chapter, "DMT is Everywhere." Let's not repeat it here.

In the early clinical studies of DMT and DET, frequent
use was made of schizophrenic patients, in the belief that if these
drugs imitate the mental disorder in normal subjects, the use of
schizophrenic population might be especially informative, either
through some enhanced response or a loss of effect. One clinical study
with a group of female patients (with 1.0 or 1.5 mg/Kg DMT being
administered, presumably by intramuscular injection) showed a delayed
onset (doubling of time), a relative freedom from autonomic effects,
and an absence of hallucinations. I truly admire the logic patterns
that allow the construction of a research study that will have it
either way. Positive effects, our hypothesis is supported. Negative
effects, out hypothesis is supported. Do schitzys get better or do
they get worse? See? We were right.

A study conducted on 40 normals, this in Hungary some 30 years ago,
found that the administration of 40 mg quantities to be symptom
free. With several of the experimental subjects in this study, the DMT
was preceded by the administration of 1-methyl-d-lysergic acid
butanolamide (UML-491), a potent serotonin antagonist. This was given
either orally (1-2 mg 30 to 40 minutes before) or intramuscularly (0.5
mg 10 minutes before). This served to greatly intensify the effects of
the DMT, with intense and agitated hallucinations, highly intensified
colors, and a more extreme loss of time and space perception. It was
assumed that UML-491 was inactive, but recent trials indicate that
there can be central effects produced. It is discussed in the entry
for LSD.

DMT is the only psychedelic tryptamine that has recently been taken
through the Kafkaesque processes for approval for human studies (via
the FDA, the DEA, and the other Health agencies of the Government) and
is one of the few Schedule I drug that is being looked at clinically
in this country today. It has been studied in New Mexico, in
Albuquerque. The first published results of this study show a smooth
grading of subjective effects as a function of injected dose. The
lowest dose (i.v.) was 0.05 mg/Kg, about 4 milligrams, and it could
not be distinguished from placebo. At 8 milligrams, there were the
physical effects without the mental. At 15 milligrams (the threshold
psychedelic dose) nearly all subjects had visual hallucinations, but
the auditory changes were rare. At 30 milligrams, the effects were
overwhelming both in speed and in intensity. The rush, the
freight-train as several subjects call it, was well underway well
before the 45 second infusion was complete. A study of repeated
administrations of dosages of 16 mg i.v., at half-hour intervals, were
made to explore the possible development of tolerance, showed that
there was none observed.

Thanks to the existence of ever-increasingly sensitive scientific
instruments, the search of body fluids for possible psychedelics has
brought forth a number that appear to be natural components of the
human animal. DMT has been reported to be in the urine of
schizophrenic patients, and so have 5-MeO-DMT, bufotenine, and its
demethylated homologue N-methylserotonin. The levels are increased
with the administration of monoamineoxidase inhibitors. A methylating
enzyme has been found in blood, capable of forming DMT in plasma, and
it is present in both normal subjects and schizophrenics. It is not
surprising that studies comparing DMT blood levels between patients
(psychotic depression, acute and chronic schizophrenia) and normal
subjects have shown no differences.

In the definition of DMT either as an endogenous psychotogen or,
equally appealing, as a natural neurotransmitter, it would be
desirable to show that the body does not build up tolerance to it
(otherwise the psychotic would spontaneously repair, and the brain
would spontaneously shut down). To address this, four subjects were
given some 50 mg of DMT intramuscularly, twice daily, for 5 days. The
blood levels that were achieved, and the picture of autonomic effects
(both in mydriasis and in cardiovascular function) were not
changed. No tolerance was seen. The psychological conclusions were a
little bit less convincing. Several said that the "high" was
diminished, but others seemed to feel a maintenance of subjective
responses. The jury is still out on this one.

The principal reason that DMT must be administer parenterally is its
rapid and efficient metabolism. It can be oxidized to the N-oxide. It
can be cyclized to b-carbolines, both with and without an N-methyl
group. It can be N-dealkylated to form NMT and simple tryptamine
itself. Best known is its oxidative destruction, by the monoamine
oxidase system, to the inactive indoleacetic acid. There is a wild
biochemical conversion process known for tryptophan that involves an
enzymatic conversion to kynurenine by the removal of the
indole-2-carbon. A similar product, N,N-dimethylkynuramine or DMK, has
been seen with DMT, when it was added to whole human blood in
vitro.

Several simple substitution derivatives of DMT are known. Those that
are known to be psychedelic have their own recipes, of course, but the
others will be summarized here. The 1-methyl homologue of DMT
(1,N,N-trimethyltryptamine) can be prepared from DMT in KOH and DMSO,
with CH3I. It forms a picrate salt which melts at 175-179 °C, and
bioxalate, mp 174-176 °C. It is more toxic than DMT in rats, but
has an identical serotonin binding capacity. The compound with a
methoxy group substituent at the 1-position is called Lespedamine,
1-MeO-DMT. With an NO bond, this should be classified as a substituted
hydroxylamine. I would love to know if anyone anywhere has ever tried
smoking it. I suspect it might very well be active, but it is, to my
knowledge, untried. I wonder why it deserves a trivial name, vis.,
Lespedamine? Two additional ring-substituted derivatives of DMT come
from the marine world. 5-Bromo-DMT and 5,6-dibromo-DMT are found in
the sponges Smenospongia auria and S. echina resp. I
have no idea if they are active by smoking (the 5-Br-DMT just might
be) but they are quantitatively reduced to DMT by stirring under
hydrogen in methanol, in the presence of palladium on charcoal. A very
closely related sponge, Polyfibrospongia maynardii, contains
the very closely related 5,6-dibromotryptamine and the corresponding
monomethyl NMT. I had the fantasy of trying to scotch the rumor I'm
about to start, that all the hippies of the San Francisco Bay Area
were heading to the Caribbean with packets of Zig-Zag papers, to hit
the sponge trade with a psychedelic fervor. This is not true. I refuse
to take credit for this myth.

The demethylated homologue is N-methyltryptamine (NMT) and it is also
widely distributed in nature. It has a synthesis in an entry of its
own.

Both the N-hydroxy and the 2-hydroxy analogues of NMT are found in
another legume Desmanthus illinoensis, but have not been
pharmacologically evaluated. Another provocative mono-alkyl analogue
of DMT is N-cyclopropyltryptamine, made from indole-3-oxalylchloride
and benzyl cyclopropylamine with eventual hydrogenolysis of the benzyl
group; mp 180-182. This compound, as with the 5-methoxy and the
7-methoxy counterparts, is a potent monoamineoxidase inhibitor, and it
has also been reported to have hypoglycemic activity. The
2-methyl-homologue of NMT was made from
2-methyl-3-(2-bromoethyl)tryptamine and methylamine. This is 2,Me-DMT
(or 2,N,N-TMT). Both it and tryptamine itself (T) have their own
entries.

Before this is closed, a couple of points need be made regarding
nomenclature. Older literature uses alpha for the 2-position of the
indole ring. Thus, alpha-methyltryptamine, in early literature, refers
to the indole-2-methyl, not to a side-chain methyl
derivative. Throughout TiHKAL, the numbers are devoted to the indole
ring, and the alpha and beta terms to the side-chain. And the use of
the letter N refers to the side-chain amino nitrogen atom. The pyrrole
nitrogen is the indole position 1.